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In this episode, Michael Koenig speaks with Greg Keller, co-founder and CTO of JumpCloud, about identity access management and why it’s becoming one of the most important operational systems in the age of AI.

Greg explains how traditional identity systems were designed for office-based companies running Microsoft infrastructure and why that model broke as companies moved to SaaS, cloud infrastructure, and remote work.

The discussion then turns to the next big shift: the rise of AI agents and synthetic identities inside organizations.

As companies deploy more AI tools, the number of machine identities may soon outnumber human employees. Managing what those systems can access will become a critical security and operational challenge.

What a CTO actually does

Greg explains the different types of CTO roles and how technology leaders help companies anticipate where the market is headed.

Identity Access Management explained simply

IAM answers three core questions inside every company:

Who are you?

What can you access?

How is that access managed?

Why the old IT model broke

Traditional identity systems were built for on-premise offices and Microsoft infrastructure. Modern companies now operate across:

SaaS applications

cloud infrastructure

remote work environments

multiple operating systems

How JumpCloud approaches identity

JumpCloud was built to manage identity across devices, applications, and infrastructure regardless of platform.

Where Okta fits in the ecosystem

Okta helped modernize browser-based authentication through Single Sign-On, while JumpCloud focuses on broader identity infrastructure.

Why COOs should push AI adoption

Greg argues AI adoption is no longer optional. Companies must encourage teams to improve productivity and efficiency using AI.

The rise of synthetic identities

AI agents, bots, APIs, and service accounts are becoming new actors inside companies that require identity governance.

Bots may soon outnumber employees

Organizations will soon manage more machine identities than human ones.

AI as a potential insider threat

AI systems can become security risks if they are granted excessive permissions or misinterpret policies.

The API key governance problem

Many AI integrations rely on API keys, which are often poorly managed and can create hidden security risks.

As companies adopt AI, identity access management becomes the control layer that determines what both humans and machines are allowed to do inside the organization.
The companies that manage identity well will move faster and operate more securely.

Links:

Michael on LinkedIn: https://linkedin.com/in/michael-koenig514

Greg on LinkedIn: https://www.linkedin.com/in/gregorykeller/

JumpCloud: https://jumpcloud.com/

Between Two COO’s: https://betweentwocoos.com

Episode Link: https://betweentwocoos.com/ai-agents-identity-access-greg-keller

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Guest: Seth Levine

Book: Capital Evolution

Podcast: Between Two COOs

Host: Michael Koenig

• Why Seth wrote Capital Evolution and why now
• Why today’s economic shift is structural, not cyclical
• How power has moved from public institutions to businesses
• What companies are being asked to carry that they weren’t built for
• How AI fits into this broader realignment
• Early signals that companies are adapting well to AI
• What strong executive teams do differently during uncertainty
• Common leadership traps when change happens too fast
• A real crisis from a portfolio company and what the executive team did well
• The new leadership muscle operators need for the next decade

00:00 – Introduction

01:40 – Seth’s 30-second pitch for Capital Evolution

04:05 – Why this shift is structural, not cyclical

07:20 – What’s broken in the current economic model

11:00 – The power shift from government to business

15:10 – What leaders are quietly losing

18:45 – Where AI fits into this realignment

23:30 – What boards see when AI adoption works

28:05 – How strong executive teams handle uncertainty

33:40 – Leadership traps during rapid change

38:10 – A crisis inside a portfolio company

44:00 – The new muscle operators must build

48:50 – A moment Seth never thought he’d see

Get Brad's new book, Give First.

00:00 — Cold open: “Something new is fucked up in my world every day”

02:00 — The Yoda t-shirt story + the mythology of Brad Feld

04:00 — “Give First” vs. “Pay it Forward”: philosophy, not obligation

07:00 — Why giving isn’t altruism — and how it works in complex systems

10:00 — Positive-sum vs. zero-sum: tennis, trust, and long games

13:00 — Does giving create outcomes, or just energy?

16:00 — Why Brad writes books: longform thinking as meaning-making

20:00 — Searching for meaning through mentorship and reflection

23:00 — “I hate the phrase pattern recognition” — mentorship done right

28:00 — The power dynamic between founders and mentors

32:00 — Management through commitment, not control

35:00 — Agile as an operating system for accountability

38:00 — Emotional intelligence and the role of executive coaches

41:00 — Mentor vs. coach vs. therapist vs. advisor

45:00 — Trust as the foundation of all high-leverage relationships

47:30 — Wild story: when the second floor of Sphero’s building collapsed

52:00 — “They can’t kill you and they can’t eat you” – Len Fassler’s advice

55:00 — Closing thoughts on being the Bill Murray of venture capital